


My Smutty Valentine Wincest/J2 Edition

by brothersbydayloversbynight (leatherwhiskeycoffeeplaid)



Category: Supernatural, Supernatural RPF
Genre: Anal, Anal Fingering, Anal Play, Anal Sex, Bondage, Condoms, Dry Humping, Fluff, Fluff and Smut, Incest, J2, M/M, Oral Sex, Rimming, Sibling Incest, Threesome - F/M/M, Unsafe Sex, Weecest, Wincest - Freeform
Language: English
Status: Completed
Published: 2018-12-16
Updated: 2018-12-16
Packaged: 2019-09-20 13:13:04
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 22
Words: 3,864
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/17023242
Author URL: https://archiveofourown.org/users/leatherwhiskeycoffeeplaid/pseuds/brothersbydayloversbynight
Summary: My smutty Valentine Wincest/J2 edition from my sideblog on tumblr brothersbydayloversbynight





	1. Wincest

Digging his fingers in deeper, Dean pulled back before slamming himself back into Sam’s stretched hole.

“You don’t even see how much I missed you.” Dean’s words punched out of him with every smack of his hips. “How every day I spent in that hell hole, fighting to stay alive with Benny, was just me trying to get back to you. Back to this.”

Dean pulled Sam back against him, using the strength in his arms to pull his baby brother up onto his knees, back to chest, Dean’s hands wrapping around Sam’s middle to hold him in place.

“Benny was nothing compared to you. He didn’t taste like you, smell like you, feel like you or fuck like you. He never took your place.” Dean dropped his right hand down, gripping Sam’s cock and fisting it rapidly. “Never took your place in my bed or in my heart. I’m yours, baby boy just as much as you’re mine.”


	2. Wincest

Sam finished tightening the brown leather belt before stepping back to inspect his handy work. “Beautiful,” he whispered to himself.

In front of him on the floor was Dean, naked, bound by the leather around his wrists, his back to Sam, and waiting for his directions.

“Present to me, big brother.”

Dean felt a shiver run down his spine and he instantly leaned forward until his face was pressed into the carpet, his cock hard and leaking, untouched between his thighs.

“That’s a good boy. You really are good at following directions, aren’t you, big brother?” Sam strolled closer, reaching down to thread his fingers through the long hair along the top of Dean’s head, gripping it tight and pulling his head back.

“Yes, sir. Anything for you, sir,” Dean breathed, his breaths coming in fast pants and his cock twitched in his lap.

“I thought as much. Dad’s perfect little soldier is now mine and what a good boy he is.”


	3. Wincest

Dean slide his fingertips into the back of Sam’s boxer briefs, the red plaid held snug against his brother’s ass making his fingers flex and pull Sam in closer to rut their cocks together through the fabric.

“This underwear is ridiculous, Sammy.”

“Shut up,” Sam grunted, his mouth catching Dean’s again and sucking his brother’s plush bottom lip in between his teeth. He rolled his hips, his balls dragging over the length of Dean’s cock and making his big brother moan into his mouth. “I like them.”


	4. Wincest x Reader

Dean worked double time, fucking himself down onto Sam’s covered cock before pounding up into your swollen cunt. The three of you had been at it for hours, the witches spell not even close to wearing off as you fucked each other.

You clawed at Dean’s chest, your pussy vibrating around his length with every brush of his cockhead against your g-spot as you perched in his lap backwards. Soft moans fell from your lips just as curses fell from Dean’s. Sam had a tight hold on Dean’s waist, guiding every bounce of his brother on his cock and making sure he hit just right inside Dean’s greedy hole.

“That’s a good boy, Dean. Make us cum. Squeeze my cock, yeah, just like that.”

Dean clenched as he fucked himself up into your cunt, the sharp snap of his hips driving you closer to the edge of your fifth orgasm of the night.

“Shit, Dean! I’m gonna cum. Fuck, fuck, FUCK!” you screamed, an intense wave washing over you and making you pull Dean over too.

The flutter of the walls of his ass squeezed Sam and he pounded up into his big brother a couple more times before cumming with a roar.

The magic that had floated through your blood streams slowly leaking out as you came inside one another.


	5. J2

Sending his best friend away from Rome to go home had eaten Jensen up inside and he couldn’t wait for his flight to finally bring him home to Texas. When he was finally home, he was greeted by Jared’s wife with a kiss to the cheek and a silent finger towards Jared’s studio.

When Jensen opened the door, he found Jared shuffling through a box, looking for who knows what and it was only when the door clicked with it’s lock did he finally realize he was no longer alone.

Jensen crossed the room in two strides and wrapped his arms around his boy. “I’m home now, baby. It’s gonna be okay.” Jensen soothed Jared for several minutes before pulling away to kiss his sweet lips.

“I’ve missed you, Jare. I’ve missed you so much and I’m so happy that you are okay.”

Jared shook his head, “I’m not ok, Jens.”

“I know, baby. I know but you are on your way to healing. While you’ve been gone there was one thing I wanted to do that I know will cheer you up. Take your pants off, Jared.”

“Jens, I’m not really…”

“Take them off and turn towards the wall.”

Jared’s eyes lit up and he dropped the track pants he’d been wearing down to the floor and turning to face the bare wall behind him.

Jensen dropped to his knees and placed a hand on each cheek of Jared’s ass, spreading him open before delving in, tongue first.

“Fuck, Jen. You did miss me.”


	6. Weecest

Sam would never get used to the feel of his big brother’s fingers pulling the cheeks of his ass apart and burying his face in his backside. The broad strokes of Dean’s tongue against his pink hole, tracing the rim, working him open until Dean could lick inside. It was overwhelming, how good it felt and how bad it felt. This was his brother, he shouldn’t want this but he couldn’t bring himself to say no. He was in love and desperately horny and Dean was the only one he wanted that could satisfy him.

So he laid flat on his belly, thighs spread enough for Dean to fit between and he watched over his shoulder, face red and covered in sweat from how good his big brother was making him feel. Yeah Sam wouldn’t get used to it but he would relish in it forever.


	7. Weecest

“I can’t Sammy. You’re too young but God do I want to.” Dean rubbed at the bulge in his jeans leftover from his makeout with Sam only moments before.

“Please Dean? Just fuck me a little?”

Shaking his head, Dean backed away from the bed, the back of his knees hitting an old kitchen chair and taking the full weight of him as he sat. “We can’t, Sam, not until you’re legal.”

Thinking quickly, Sam stood from the bed and started pulling off his clothes. “You can’t fuck me but you can watch.”

“Watch?”

Sam nodded, his overgrown hair falling around his face as he crawled sideways onto the ratty old mattress. “Watch me play with myself. Get myself open and ready for you. Make myself cum for you.”

“Damn it, Sammy.” Dean grunted to himself, his right hand squeezing the erection in his jeans to no relief. “Do it.”

Turning on the bed so his ass faced his brother, Sam dropped a shoulder to the cushion and reached between his legs, his right hand stroking his balls out of the way, his cock chubbing up as he licked his own fingers. With practiced precision, Sam brought his spit slicked fingers back around and rubbed them over the pink of his hole.

Dean groaned at the sight, his baby brother rubbing and dipping his fingers into his virgin hole, spreading himself open to the one man he was going to ever let in.

“Jesus, Sammy I can’t wait for your birthday.”


	8. Weecest

  
The door to the motel shut firmly and the boys waited until they could no longer hear the sound of the Impala’s engine before tugging off all of their clothes. It had been almost a month since they had been able to be alone together and it was becoming harder and harder to hide their need for each other.

Dropping to his knees as soon as he was naked, Dean crawled over to Sam, pushing his ass back against the linoleum kitchen table, yanking the sweats he still wore down his thighs to see the hardened length underneath spring free.

Licking his lips in hunger, Dean reached for the thick cock, sucking the crown into his mouth to swirl his tongue over, re-familiarizing himself with the taste of his baby brother.

“So good,” he moaned, swallowing down Sam’s shaft, bobbing his head up and down the heated flesh and working his brother’s cock like a seasoned pro.

“Fuck, Dean, I’ma cum already, shit,” Sam grunted above him and Dean was okay with that.

“Go for it, Sammy. Cum down my throat so I can open up that pretty little cunt of yours and fuck you hard like you need.”


	9. Weecest

“Someone’s gonna see us,” Sam hissed, his clothes already spread out on the concret of the patio they were hiding in.

“No, they won’t. Everyone is at work or school. You wanted to ditch, so we’re ditching.” Dean nippled at Sam’s bare shoulder, lube already shiny on his index and middle finger as he pressed them to Sam’s wrinkled opening.

A soft gasp from Sam’s pink lips followed and it wasn’t long until he was fucking himself back onto Dean’s hand.

“Ready for my cock, baby brother?”

Unable to form words, Sam nodded bracing himself against the brick column in front of him and sticking his ass out towards Dean.

Bending his knees just slightly, Dean notched his cock at Sam’s entrance and pushed forward, pulling his hips back to bring them both together with a grunt. When he was fully seated and Sam had adjusted to the intrusion inside him, Dean started a punishing pace.

“See, Sammy. No one to catch us in the middle of the day.”

Sam mewled, his right hand reaching to tug on his semi-hard cock. “Maybe we should ditch more often.”


	10. Weecest

“Is this okay?” Sam asked, his voice soft and timid.

“It’s so good, baby boy. You are doing amazing.” Dean praised, his baby brother bouncing up and down on his latex covered cock. “You were made to do this, Sammy. How does it feel, baby?”

Sam’s fingers dug into Dean’s biceps, his legs getting tired from bouncing and starting to rock back and forth instead, Dean’s cock hitting his prostate with each movement. “Feels good, De. Really, really good.”

Dean trailed his hands up and down his brother’s sides, enjoying the smoothness that came with the body of a 17 year old. “Good, so good.”

“Dean?”

“Yeah, baby boy?”

Sam bit at his bottom lips, his hips still rocking as he looked down into his brother’s jade eyes. “Can you touch my cock? Please?”

Dean smiled, bringing his right hand up to his mouth and licking his palm before lowering it down between their bodies and taking hold of Sam’s stiff cock. “Anything for you, baby boy.”


	11. Weecest

“This is okay, right Dean?”

Dean ran his palms over the insides of Sam’s thighs, his legs bent and in the air as Dean laved his tongue down from Sam’s cock to his relaxed balls, licking farther south towards his taut rim.

“Yeah, Sammy. It’s okay. Did you want me to stop?”

Sam shook his head, his overgrown locks shuffling around his face. “No, I just never thought about doing this before.”

Dean kissed the inside of Sam’s calf before turning his gaze onto Sam’s face. “It’s okay you haven’t thought about it before. I’m gonna show you how good it feels. Just relax for me baby boy.” Lowering his lips to his brother’s asshole, Dean licked a strip between the crack, focusing on the ring of muscle in the center.

Sam lay still above him, eyes trained on where his big brother knelt licking him open. Oh, Sam had thought about this plenty but he never thought he’d actually get Dean to rim him.


	12. Weecest

Sam hadn’t waited a full five minutes after dad left before pulling off Dean’s clothes and pushing him onto the bed Sam had been sleeping in alone all week.

“Need you,” he muttered, tearing his shirt off and dropping between his brother’s bowed legs. He wrapped his fingers around Dean’s semi hard length and sucked the head into his mouth, his pink lips happily sliding up and down his big brother’s cock.

“Jesus, Sammy. Miss me?” Dean joked before groaning loudly as Sam’s lips pushed down his shaft until his nose was pressed against Dean’s pelvis.. “Shit, Sammy.” Thick fingers carded through Sam’s long hair, bobbing up and down as Sam sucked at Dean’s cock in a ravenous frenzy.

Drool puddled at the base of Dean’s cock, obscene slurping noises filling the room and leaving Dean fascinated at how focused Sam was at sucking him off. As Sam hollowed his cheeks, Dean gave up on watching and just laid back against the mattress, a goofy grin on his face as his baby brother sucked him dry.


	13. J2 x Reader

Jensen made the prettiest sounds when Jared fucked him, his cockhead punishing Jensen’s prostate, milking him as you held firmly to the root of his cock. Hot white leaked steadily from the slit of his painfully hard tip, coating your fingers as you lapped at it with your tongue.

The sticky line running down Jensen’s sack and onto Jared’s thighs only spurred on the three of you. Jared fucking in deeper, harder, leaving bruises on Jensen’s frame with his lips and teeth, his own cock pulsing out ropes of his own release into the condom that contained him. The jerks from Jared’s cock pushed Jensen even farther, a large gob of cum shooting up and landing along your swollen lips.

“Look at the mess you made, Jens. Someone needs to clean it up,” you purred, jerking his cock as you rose to your feet, your mouth colliding with his to lick clean of his spunk.

“Mmm,” he hummed happily, licking his release from your face as his cock finally lay spent in your fist and Jared could pull free from his abused hole.


	14. J2

This was the dream, Jared’s pink and stretched hole, opening and greedily sucking in Jensen’s bare and lubed cock. The rim fluttering around the head as it pulled itself around the ridge to shut over his shaft. There was nothing hotter for Jensen and he pushed slowly, his cock disappearing and reappearing from the eager depths of Jared’s ass over and over again.

If Jensen could ask to repeat any day or moment of his waking life into his dreams, it would be this one. He’d make wet patches all over his crisp white sheets if it meant he could relive that first slide of his cock into Jared’s ass. The resistance it gave before finally giving way, Jensen’s cock swallowed whole while Jared made that breathy gasp underneath him. It was perfect and like a dream and thank god it was reality.


	15. Alpha!Jared x Omega!Jensen

“Such a good little Omega. You ready for my knot, baby? Ready for your Alpha to breed you, Jens?” Jared slowed his pace, his knot semi popped and tugging on Jensen’s heat slicked hole.

“Yes, fuck, Jare please. Breed me and fill me with pups. Need your knot,” he begged withering on Jared’s length, slick gushing out and around his Alpha’s cock.

“It’s ok, Omega. Gonna breed you nice and deep. Here it comes, baby. Here it, fuck!” Jared growled, his knot popping and slamming passed Jensen’s rim, locking him inside to pump enough cum into him that Jensen’s belly would swell.

For the next half hour, Jared’s cock pulsed out cum until Jensen was a whimpering mess, so full his belly was already round yet as far as they knew not pregnant.

“You are gonna make such a beautiful pregnant Omega. Can’t wait to see this belly round for real. I’m gonna pull out now, okay Jen?” Jared padded Jensen’s sweat slicked hair behind his ear and kissed the side of his head.

“It’s ok, just go slow so I don’t loss too much.”

Jared laughed, pulling out and seeing a gob of his cum fall from his Omega’s puffy hole. “Don’t worry about that, baby. I pumped most of it in pretty deep.”


	16. J2

The car would be there in twenty minutes but that was more than enough time as Jensen threw a leg over Jared’s lap. His cock standing tall and slicked as Jensen held his cheeks open and sank down over him.

Jared stretched him out perfectly and Jensen glanced at the clock quickly before rolling his hips, grinding against Jared and fucking them both towards a release that would keep them satisfied through the con weekend.

They never had time to fuck while doing a convention so this pre-con fuck had to be the best. Jensen kept Jared deep, rocking on his co-stars cock like a bitch in heat as Jared thrust up into him. If there was one thing Jensen wanted the most before they left, it was an ass full of cum that made him ache until Monday.


	17. J2

“Jeez, Jare. Slow down.” Jensen mumbled watching as Jared let his semi hard cock spring free of his grey sweats.

“No, been thinking about this all day.” With greedy hands, Jared lifted Jensen’s cock to his pink lips, kissing the head before sucking the velvet tip into his mouth.

“Fuck, yeah, okay man, go for it.” Jensen relaxed back into the recliner in his trailer and let Jared swallow down his cock, feeling it fatten up and twitch against the muscle of Jared’s tongue. That same tongue that traced the vein on the underside all the way down to his sack to lick while Jared’s throat clenched with a couple swallows, deep, wet squelches coming out around Jensen’s cock.

Threading his thick fingers into the long strands of Jared’s hair, listening to him hum happily around the cock he bobbed his mouth up and down on, Jensen sighed, “Yeah, you do whatever you want, baby boy. You just do whatever you want.”


	18. Alpha!Jensen x Omega!Jared

He had been sweating buckets through the whole afternoon panel, even more than usual and as soon as he was free from the eyes of fans, Jared grabbed Jensen, his Alpha, by the wrist and took off for the private green room they had.

“Okay, Omega. It’s gonna be okay. Talk to me.” Jensen pulled his hand free and reached up to cup Jared’s clammy face.

“Need your knot, Alpha. I can’t wait anymore.” Jared whined nuzzling into Jensen’s palm and pressing a kiss to the smooth skin.

“Jare, we don’t have enough time for me to knot you.”

“Yes, you do.” Jared’s hands fell to Jensen’s belt, flicking it open and releasing the button in record time. “I need a knot or I’m not going to be able to do anything else today. We have so much and it hurts so bad. Please, Jensen? Please, Alpha?”

Jensen licked his lips before nodding. “Present, Omega.”

Jared spun around his hand undoing his pants and pushing them down to expose his sopping wet hole. He planted his hands firmly on the white snack table in front of him and spread his legs enough to give his Alpha room to stand behind him.

Jensen’s hands smoothed over the globes of Jared’s ass before pulling down his zipper and giving his cock a few pumps, his thumb stroking the knot at the base that was still loose and waiting for his Omega’s eager hole.

With a hitch of his breath, Jared cried out as Jensen sunk his cock into his aching channel, the rough scratch of Jensen’s jeans scraping against his skin as his Alpha started to thrust. It was quickly paced, the table Jared had his hands on knocked against the wall repeatedly as Jensen fucked into him.

“Sorry this has to be quick but we have autos to get to. I’m not going to knot you but I will cum inside you. That should be enough to hold you off until tonight.”

Jared threw his head back, his hair whipping back with him. “Yes, please Jen, anything. Just make it stop.”

Holding on tight, Jensen growled, “get ready, Omega, gonna fill you up.”


	19. J2 x Reader

Jared whimpered above you as you sucked his monster sized cock down your throat, in his ass was Jensen, balls deep and hammering away.

“Shit,” the giant of a man cursed to himself as you sucked a bit harder, your mouth moving up and down the shaft quicker.

“She feels good doesn’t she, Jare? The best mouth money can buy. You gonna cum down her throat while I fuck your ass raw?” Jared didn’t reply, he just held on for the ride as Jensen pounded up into him. “Come on, sweetheart, you gotta talk to me.”

“Fuck, Jay, she feels good, you feel good. Fuck, I’m gonna cum, oh shit.”

Rope after rope of thick white shot down your throat and you swallowed it down as quick as you could. When you were able to pull away, Jensen was slipping out of Jared’s abused hole and tearing the used condom off.

“Come over here and finish me off, gorgeous. Jared can help show you how.”


	20. J2

“God, I fucking missed you,” Jared growled, nipping at Jensen’s full bottom lip and skimming his hands down his boyfriend’s freckled back.

“Miss you too,” Jensen muttered, rutting himself against Jared, his cock swelling just as quickly.

Jared’s hands reach farther down, finding Jensen’s round and perfect ass, squeezing it tightly and pulling his hips in closer, if that was even possible.

Their tongue battled for dominance and they both rubbed their clothed cocks together, wetting the front of each other shorts, not even caring about the stains later.


	21. J2

Jared’s hand was perfect for rubbing their cocks together. His long fingers encompassing both his and his co-star’s length, spreading their pre-cum down their shafts as he thumbbed over their slits.

It felt incredible, neither one of them doing anything but laying together and having Jared jerk them both off. The sensitive underside of their cocks glided over one another, making Jensen’s belly twitch and Jared’s asshold flutter. They knew this was just foreplay but fuck did it feel good.


	22. J2

  
They still hadn’t put the curtains up in their new home but Jared already had Jensen on his back, legs in the air with his boxers around his knees.

“Fuck you look sexy on that white couch. Like sin incarnate.” Jared murmured, his lips sucking down each of Jensen’s thighs until he could lick his way into his boyfriend’s still wrecked hole from the night before.

Keeping his hands firmly planted on the plus cream carpet, Jared went to town, licking and sucking at Jensen’s reddened rim, Jared’s cum from the night before still leaking out from him. Growls of passion left Jared’s mouth as he devoured Jensen’s asshole, getting him ready for what was to come next.

Pulling away, his lips slick and red from the last fifteen minutes of eating Jensen out, Jared asked, “think it’s time to break in the new sofa and make you ride my cock.”


End file.
